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Can You Wear Chelsea Boots with Jeans? 7 Best for 2023

Last updated: February 2, 2023

By: Miles HenryFact Checked

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Chelsea boots have become a go-to style for many people looking to add some edge while staying stylish and comfortable. An equestrian friend purchased a pair but isn’t sure they’re appropriate to wear with jeans, so we decided to check the latest trends.

Chelsea boots are an excellent option to wear with your favorite jeans. They work with both formal and casual attire because they have just enough ruggedness that’s not too overbearing but still adds personality.

Chelsea boots are an ideal addition to any wardrobe for men and women. You can wear them with a wide range of outfits, from casual business attire to dresses to business attire. However, some people still wonder if it’s appropriate to wear Chelsea boots with jeans.

Picture of a woman wearing chelsea boots with jeans.

The answer is yes – you can definitely mix these two together. Read on for some tips on how to pull off this look.

In this guide, we will talk about the following:

What Are Chelsea Boots?

Chelsea boots have been in vogue since 1837. They are characterized by elastic panels on their sides and a little pull-on tab on the back, making them very easy to get on and off.

Men and women can both wear Chelsea boots, and they are especially a favorite riding boot of equestrians. 

Chelsea boots are classic and compact boots that have been around since the Victorian era. They are characterized by an elastic panel on the side which makes them fit snugly despite not having laces.

The close-fitting boots are ankle-high and feature a fabric tab or a loop. This helps the user pull the boot up easily while wearing them.

7 Best Chelsea Boots to Wear with Jeans – 2022 Top Picks

Many top brands offer Chelsea boots, and below are my top 7 picks:

#1. Best Chelsea Boots for Men: Bruno Marc Suede Leather Chelsea Boots

I ALWAYS GET COMPLIMENTS when I wear my Bruno Marc suede leather Chelsea boots with jeans. They look stylish and elegant and are also very comfortable. I find them well-made and durable, but I don’t ride horses with them because they’re suede.

I recommend ordering a size down in the Bruno Marc Chelseas; they tend to run a bit large. Also, they will break in and fit your feet the more you wear them.

You will love the fact that they are available in so many colors, so you get the choice of wearing them with blue or black jeans.

Like traditional Chelseas, Bruno Marc Chelsea boots feature iconic elastic side stretch bands and a back-front fabric tab. This makes it very easy to wear and remove them. Over 8,000 customers reviewed these boots and rated them highly.

Here are some more features of the Bruno Marc Chelsea boots:


  • Sturdy sole with suede-leather uppers
  • Soft EVA foam to cushion the feet
  • Thermoplastic outsole with tread to prevent slipping
  • Available in 9 awesome colors


  • High-quality materials, excellent construction
  • Plenty of color choices
  • Great price!


  • While they hold up to rain, snow, and slush, they tend to fade a bit after use. (See the expert tip below to prevent this).

Expert Tips

  • Treat them with this protective suede boot spray. It will keep your boots looking great for a long time.
  • Use silicone gel inserts if the boots loosen up over time.

How they compare

Bruno Marc Chelsea boots are comparable with Beckett-Simonon’s high-end Chelsea boots but nearly 1/4th the price.

They are available in 9 attractive colors, so you can look elegant in dark or light-colored jeans. They also help in keeping your feet warm when riding in winter. Their construction is remarkable, and they only use high-quality materials.

Bruno Marc boots are stylish and versatile enough to wear with formal or semi-formal attire. You will surely receive many compliments on them.

#2. Best Women’s Chelsea Boots: Dr. Marten’s RomettyII Chelsea Boots for Women 

When I bought my daughter these as a surprise present, she was thrilled. Dr. Martens is one of her favorite brands, and these Chelsea boots hit the mark.

Dr. Marten’s women’s Chelsea boots have been a major hit since they were first introduced in the 1970s, and this is primarily due to their classic design that you can wear with anything from jeans or skirts and all year round.

In the decades since, the brand has come up with a diverse range of Chelsea boots for women with features like a 1 1/8th inch platform and a towering 2 1/4th inch heel.

Dr.Martens RomettyII Chelsea boots strike the perfect balance between feminine and tough and are ideal for pairing with jeans and other casual or formal dresses.

My wife wears them with jeans and riding pants and claims that it is the most comfortable pair of boots she has ever owned.

Here are its other features


  • Feature Dr. Martens’s signature yellow stitching, heel loops, and grooved edges.
  • Packed with plenty of rugged features making it the ideal riding boot.
  • It comes with a pull-on tag and zip for easy on/off and snug fit
  • Cemented sole – sole is cemented to the upper
  • Air-cushioned sole
  • Uppers made from 70% leather and 30 % elastic inner


  • Comfortable and stylish
  • It can be worn with thick riding socks


  • Tend to run big
  • Pricier compared to many brands.

Expert Tips

How they compare

Dr. Martens Rometty Chelsea boots have a sleek silhouette that is modern yet classic. The price may be on the higher side, but it is totally worth it! They don’t need to be worn in and soften up quickly. The Rometty Chelsea is comfortable, long-lasting, and fits well. It is sure to make an excellent gift for the equestrian woman in your life.

#3. Best Unisex Chelsea Boot: Amoji Unisex Ankle Chelsea

Amoji Unisex ankle Chelsea boots are perfect to pair with jeans or shorts on rainy days. They are 100% waterproof, easy to clean, and also feature the iconic tab on the back for easy on/off. 

You can wear these unisex boots with jeans, shorts, or any other casual or formal pants.


  • 100% waterproof
  • Slip-resistant soles


  • Stylish
  • It can be worn above or below the pants
  • Supportive, soft
  • Unisex
  • Available in 7 great colors and 9 men’s/women’s sizes


  • Caused chafing at the ankles in some users

Expert Tips

  • Amoji Unisex ankle rain Chelsea boots run large, so order a size down.
  • They are unlined, so it helps to wear a comfy pair of socks with them.

How they compare

Amoji Unisex ankle rain Chelseas cost less than $50. They are stylish, durable, and perfect for wet weather riding. You can pair them with jeans, shorts, skirts, or business attire.

#4. Best Dressy Chelseas for Men: Deer Stags: Rockland Memory Foam Chelsea Boot

Are you looking for stylish and dressy boots to wear with jeans, pants, or formal attire? You will love Deer Stags Chelsea boots which feature 100 percent smooth leather uppers.

They come with removable memory foam insoles, making them comfortable for wearing all day. Suppose you’re looking for something a bit more elegant; take a look at GIFENNSE’s Chelsea boots. They are a little more expensive but are elegant and luxurious.

Here is a look at GIFENNSE Chelsea boots:


  • Made with high-quality genuine cowhide leather
  • Hand Painted and hand polished
  • Available in 4 stylish colors and 11 size options


  • Comfortable
  • Durable
  • Stylish


  • Not waterproof
  • They have a pointed-toe design, so they could run a bit small for some users.

Expert Tips

  • Add Dr.Scholl’s inserts for extra padding.

How they compare

GIFENNSE men’s Chelsea boots are slightly expensive compared to the other brands mentioned here. However, they are made with genuine cowhide leather and hand-painted and hand-polished. They are stylish and elegant for formal wear but can be paired with jeans – especially black ones. There could be some size issues, as reported by many users.

#5. Best Vegan Women’s Chelsea Boots: CUSHIONAIRE Sasha Chelsea with Memory Foam

CUSHIONAIRE Sasha women’s Chelseas are made using vegan leather – which means no animals are harmed during production. 

These stylish boots feature a 2-inch heel and come with premium memory foam inserts for extra padding and comfort.


  • Made with vegan leather
  • Comfortable memory foam inserts
  • Water-resistant – keep your feet dry and comfy
  • Lightweight
  • Available in 3 colors and 8 sizes


  • Stylish and comfortable
  • Do not make a squeaking sound while walking on floors
  • Suitable for wet weather.


  • Run big, so order a size down

Expert Tips

  • The white color CUSHIONAIRE Sasha Chelseas tends to scuff easily.

How they compare

For just under $50, the SASHA Chelsea boots from CUSHIONAIRE will definitely enhance your style quotient. Add them to your wardrobe to pair them up with jeans or shorts. They are stylish and super comfy due to the memory foam inserts. The durable boots are also suitable for riding in wet conditions.

#6. Best Budget Buy: Soda Pilot Women’s Chelsea Boots

Look fashionable and trendy without breaking the bank with these Chelsea boots from Soda Pilot. They are stylish, cool, and comfortable and available in several fantastic colors to go with different colored jeans.


  • Shaft measures around 5.5-inches
  • The platform measures 0.75 inches, and the lug sole stack heel is around 1.5 inches high.
  • Man-made sole
  • Wide stretchy elastic side panels
  • Available in 4 colors and 10 sizes


  • Stylish
  • Comfortable


  • Run tight, order a size up.

How they compare

Soda Pilot Chelsea boots are versatile and great for walking, hiking, horse riding, or simply running errands. They are affordable without compromising on quality. These boots will surely win you tons of compliments. Note that for most users, they ran small, so order a size up.

#7. Best Chelsea Boots for Children: Unisex Child Chelsea Boots from Deer Stags

I bought the Deer Stags Chelsea boots for my grandkids. They looked sharp and stylish in them. I recommend wearing long socks with them as they tend to rub the front part of the feet.

Deer Stags Kids Zane Chelsea booties are sure to let your young equestrian ride in style. They are made with faux leather and look great when worn with blue or black jeans. Your kids can also wear them with riding pants. The brand carries various-sized boots for children aged 4 to 12 years.

Here are some of its physical features


  • Dimensions: boot opening 10.5-inches around with shaft measuring 4.75-inches from the arch
  • Faux leather construction
  • Memory foam footbed for extra comfort
  • TPR outsole.
  • Available in 2 colors and multiple sizes.


  • Style on a budget
  • Great for kids taking riding lessons


  • The opening might be slightly narrow for some kids.

Expert Tips

How they compare

Many parents will appreciate Deer Stags’ Chelsea boots’ price. Kids outgrow their boots quickly, so not many people would want to spend too much on boots, but you want to ensure your child wears good footwear. With these, you can stick to your budget. They look stylish and will go well with jeans.

History of Chelsea Boots

Queen Victoria’s bootmaker Joseph Hall made these special boots for Her Highness in the early 1800s. He claimed that the Queen walked in them daily and advertised the boot as “J.Hall’s patent elastic ankle footwear.”

Later on, the boots became popular as multi-purpose riding boots and may have even inspired the Jodhpur boots from India. The popularity of the Chelsea boots sky-rocketed further after manufacturers started using vulcanized rubber in the elastic ankle.

The ankle height combined with elastic made the boots even easier to take off and put on. Men and women both loved the Chelsea boots, and they soon became the go-to boot for the riding community.

Why Are They Called Chelsea Boots?

Chelsea Boots were named after the Mod hub’ Chelsea – a part of the UK – where they were extremely popular and worn by both men and women.

‘Mod’ is a subculture that began in London and spread throughout the United Kingdom. It is believed that a group of young men may have ‘triggered’ the interest in the Mod scene.

These men wore fashionable ankle boots and listened to jazz. The Mods in the 1960s especially preferred Chelsea boots which were even adopted by the Beatles band in 1961.

If you’re in the market for Chelsea boots to wear with jeans, I recommend the following top picks for men and women:

Below is a YouTube video showing how men can sport a pair of Chelsea boots with jeans.

YouTube video

Key Takeaways

Chelsea boots have been around for a while and are a fashion staple for stylish men and women. This boot style rises just above your ankle and features elastic side panels with a pull-on tab that enhances the ease of wearing them. 

Both men and women should have Chelsea boots in their wardrobes to enhance their style quotient. They go great with jeans, although you can also wear them with other pants, skirts, or shorts. They also make a comfortable pair of horse riding boots.

I recommend Dr. Martens RomettyII Chelsea boots for women and Bruno Marc suede Chelsea boots for men. Do check out my other recommendations as well.

FAQs – Chelsea Boots

How to wear jeans with Chelsea boots?

The bottom edge of the jeans should sit slightly over the boots. This means that your jeans should be ankle length. Don’t tuck your jeans inside Chelsea boots; it doesn’t look good and could loosen up the boots.

How long should jeans be when wearing Chelsea boots?

The jeans’ legs’ edges should meet the Chelsea boot at the ankle. If your jeans are longer, roll them up about ½ to 1 inch to keep the ankle visible.

Can you wear black Chelsea boots with blue jeans?

Black Chelsea boots worn with blue jeans are stylish. Other colors like tan, cream, and beige are also excellent Chelsea boot colors to pair with blue jeans.

Should Chelsea boots be tight or loose?

Chelsea boots should have a snug fit – neither too tight nor too loose; they have elastic sides to keep them in place.